Triethylamine → 3,5-Di-tert-butylphenyl methanesulfonate

HRID 1037702Notes

Reaction equation

HRID 1037702 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([OH:15])[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C1(C)C=CC=CC=1>[CH3:23][S:24]([O:15][C:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=1)(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 708253,5-Di-tert-butylphenol2×

Product 1

HCID 866395023,5-Di-tert-butylphenyl methanesulfonateYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

2.50 g (0.012 mol) of 3,5-di-tert-butylphenol and 1.27 g (0.013 mol) of triethylamine were dissolved in 15 mL of toluene followed by dropping in 1.45 g (0.013 mol) of methanesulfonyl chloride over the course of 10 minutes at 5° C. Following completion of dropping, the mixture was stirred for 3 hours at 25° C. and the 3,5-di-tert-butylphenol was confirmed to no longer be present. The reaction liquid was placed in ice water and following separation of the organic layer, was washed twice with saturated brine followed by drying with MgSO4 and concentrating to obtain 3.21 g (yield: 98%) of 3,5-di-tert-butylphenyl methanesulfonate. A purified product crystallized with n-hexane (white crystals, melting point: 76° C.) was used in a battery test.

Workup

  1. customThe reaction liquid
  2. customseparation of the organic layer
  3. washwas washed twice with saturated brine
  4. dry with materialby drying with MgSO4
  5. concentrationconcentrating

Sources & evidence

ORD record
ord-5cab1da68c044954a2999520c8f9084a
Source dataset
uspto-grants-2013_10
Patent number
US08546599B2

Reaction notes

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